Hydrochloric Acid → 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360554

반응식

HRID 1360554 반응식
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:22]#[N:23])=[N:11][N:12]([CH2:19][CH2:20][CH3:21])[C:13]=1[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]1[N:12]([CH2:19][CH2:20][CH3:21])[N:11]=[C:10]2[C:9]=1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:2]=[C:22]2[NH2:23]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 669588824-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 577175341-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine수율 63.7%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Hydrochloric acid (18 mL, 71.0 mmol) in ethanol was added dropwise to a solution of 4-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile (7.50 g, 23.7 mmol) in 150 mL of ethanol. The resultant solution was heated to reflux overnight, concentrated under reduced pressure, and diluted with water. The pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate. The aqueous layer was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a reddish solid. The material was purified via flash column chromatography on silica gel (eluting with a 96:4 mixture of dichloromethane/methanol) to afford 4.78 g of 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine.

후처리

  1. temperatureto reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. additionThe pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate
  5. extractionThe aqueous layer was extracted with several portions of dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a reddish solid
  11. customThe material was purified via flash column chromatography on silica gel (
  12. washeluting with a 96:4 mixture of dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-406860c1a3494857b8df1203262b0dff
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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